This study describes how student characteristics and environmental influences experienced in high school (and the interactions among them) impact academic engagement of first-semester college students. Data, collected from 300 first-year students at a single university at two different times, showed that precollege student characteristics of academic efficacy and educational values and environmental influences of family educational culture and student-teacher interactions have both main effects and interactions on two types of academic engagement: (a) responding to class-related requirements and (b) participating in class-related initiative taking. This study suggests that academic engagement may develop iteratively over time and as an interaction of student characteristics and environmental influences experienced. In addition, the research suggests that the two types of engagement differ regarding their antecedents. Research and practical implications are discussed.